Phenacyl bromide → 2-phenylimidazo[1,2-a]pyridine

HRID 2252033Notes

Reaction equation

HRID 2252033 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C([O-])(O)=O.[Na+]>C(O)C.O>[C:5]1([C:3]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 104392-AminopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 2011362-phenylimidazo[1,2-a]pyridineYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Stir a solution of 2-bromoacetophenone (1 g, 5.024 mmol) and 2-aminopyridine (591 mg, 6.280 mmol) in ethanol (4 mL) containing NaHCO3 (658 mg, 7.837 mmol) at room temperature for 6 hours. Dilute the mixture with water (15 mL) and extract with ether (3×20 mL). Wash the combined organic layers with saturated aqueous sodium chloride (25 mL), dry (MgSO4) and concentrate in vacuo. Purify the residue by flash chromatography (SiO2; eluent:hexane/EtOAc 4:1) to give a white solid, 79% yield. MS(ES+): m/z=195.1 (M+H)+

Workup

  1. extractionextract with ether (3×20 mL)
  2. washWash the combined organic layers with saturated aqueous sodium chloride (25 mL)
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography (SiO2; eluent:hexane/EtOAc 4:1)
  6. customto give a white solid, 79% yield

Sources & evidence

ORD record
ord-45b014cde0f0452e96f4b69e9ca11642
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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